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Literature DB >> 29038742

Methylene C(sp³)-H Arylation of Aliphatic Ketones Using a Transient Directing Group.

Abstract

Palladium-catalyzed methylene β-C(sp3)-H arylation of aliphatic ketones using a transient directing group is developed. The use of α-benzyl β-alanine directing group that forms a six-membered chelation with palladium is crucial for promoting the methylene C(sp3)-H bond activation.

Entities: Chemical Disease Species

Keywords: C–H activation; arylation; ketone; palladium; transient directing group; β-amino acid

Year: 2017 PMID： 29038742 PMCID： PMC5640319 DOI： 10.1021/acscatal.7b02905

Source DB: PubMed Journal: ACS Catal Impact factor: 13.084

41 in total

1. Biomimetic hydroxylation of nonactivated CH2 groups with copper complexes and molecular oxygen.

Authors: Bruno Schönecker; Tatjana Zheldakova; Yong Liu; Manuela Kötteritzsch; Wolfgang Günther; Helmar Görls
Journal: Angew Chem Int Ed Engl Date: 2003-07-21 Impact factor: 15.336

2. The catalytic intermolecular orthoarylation of phenols.

Authors: Robin B Bedford; Simon J Coles; Michael B Hursthouse; Michael E Limmert
Journal: Angew Chem Int Ed Engl Date: 2003-01-03 Impact factor: 15.336

3. Catalytic C(sp(3) )-H Arylation of Free Primary Amines with an exo Directing Group Generated In Situ.

Authors: Yan Xu; Michael C Young; Chengpeng Wang; David M Magness; Guangbin Dong
Journal: Angew Chem Int Ed Engl Date: 2016-06-08 Impact factor: 15.336

Review 4. Towards mild metal-catalyzed C-H bond activation.

Authors: Joanna Wencel-Delord; Thomas Dröge; Fan Liu; Frank Glorius
Journal: Chem Soc Rev Date: 2011-06-10 Impact factor: 54.564

5. C-H bond activation. Regioselective ketone α-alkylation with simple olefins via dual activation.

Authors: Fanyang Mo; Guangbin Dong
Journal: Science Date: 2014-07-04 Impact factor: 47.728

6. Intermolecular amidation of unactivated sp2 and sp2 C-H bonds via palladium-catalyzed cascade C-H activation/nitrene insertion.

Authors: Hung-Yat Thu; Wing-Yiu Yu; Chi-Ming Che
Journal: J Am Chem Soc Date: 2006-07-19 Impact factor: 15.419

7. Synthesis of Fluorenones from Benzaldehydes and Aryl Iodides: Dual C-H Functionalizations Using a Transient Directing Group.

Authors: Xiao-Yang Chen; Seyma Ozturk; Erik J Sorensen
Journal: Org Lett Date: 2017-02-22 Impact factor: 6.005

8. Iridium-Catalyzed ortho-C(sp²)-H Amidation of Benzaldehydes with Organic Azides.

Authors: Delong Mu; Xinmou Wang; Gong Chen; Gang He
Journal: J Org Chem Date: 2017-04-12 Impact factor: 4.354

9. Catalytic direct β-arylation of simple ketones with aryl iodides.

Authors: Zhongxing Huang; Guangbin Dong
Journal: J Am Chem Soc Date: 2013-11-15 Impact factor: 15.419

Review 10. Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

Authors: Xiao Chen; Keary M Engle; Dong-Hui Wang; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2009 Impact factor: 15.336

13 in total

1. Versatile Alkylation of (Hetero)Aryl Iodides with Ketones via β-C(sp³)-H Activation.

Authors: Ru-Yi Zhu; Luo-Yan Liu; Han Seul Park; Kai Hong; Yongwei Wu; Chris H Senanayake; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2017-11-03 Impact factor: 15.419

2. Pd-Catalyzed γ-C(sp³)-H Fluorination of Free Amines.

Authors: Yan-Qiao Chen; Sukriti Singh; Yongwei Wu; Zhen Wang; Wei Hao; Pritha Verma; Jennifer X Qiao; Raghavan B Sunoj; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2020-05-18 Impact factor: 15.419

3. Transient Directing Group Enabled Pd-catalyzed γ-C(sp³)-H Oxygenation of Alkyl Amines.

Authors: Yan-Qiao Chen; Yongwei Wu; Zhen Wang; Jennifer X Qiao; Jin-Quan Yu
Journal: ACS Catal Date: 2020-04-24 Impact factor: 13.084

4. Distal γ-C(sp³ )-H Olefination of Ketone Derivatives and Free Carboxylic Acids.

Authors: Han Seul Park; Zhoulong Fan; Ru-Yi Zhu; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2020-06-05 Impact factor: 15.336

Review 5. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.

Authors: Bin Liu; Andrew M Romine; Camille Z Rubel; Keary M Engle; Bing-Feng Shi
Journal: Chem Rev Date: 2021-10-29 Impact factor: 60.622

6. Pd^II-Catalyzed Site-selective β- and γ-C(sp³)-H Arylation of Primary Aldehydes Controlled by Transient Directing Groups.

Authors: Yi-Hao Li; Yuxin Ouyang; Nikita Chekshin; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2022-03-14 Impact factor: 16.383

7. Pd^II -Catalyzed Enantioselective C(sp³ )-H Arylation of Cyclobutyl Ketones Using a Chiral Transient Directing Group.

Authors: Li-Jun Xiao; Kai Hong; Fan Luo; Liang Hu; William R Ewing; Kap-Sun Yeung; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2020-04-01 Impact factor: 15.336

8. Ligand-Enabled γ-C(sp³)-H Activation of Ketones.

Authors: Ru-Yi Zhu; Zi-Qi Li; Han Seul Park; Chris H Senanayake; Jin-Quan Yu
Journal: J Am Chem Soc Date: 2018-03-02 Impact factor: 15.419

9. Palladium(II)-Catalyzed Selective Arylation of Tertiary C-H Bonds of Cyclobutylmethyl Ketones Using Transient Directing Groups.

Authors: Jin-Tang Cheng; Li-Jun Xiao; Shao-Qun Qian; Zhe Zhuang; An Liu; Jin-Quan Yu
Journal: Angew Chem Int Ed Engl Date: 2022-03-09 Impact factor: 16.823

10. Exploring the mechanism of the Pd-catalyzed spirocyclization reaction: a combined DFT and experimental study.

Authors: Ivan Franzoni; Hyung Yoon; José-Antonio García-López; Amalia Isabel Poblador-Bahamonde; Mark Lautens
Journal: Chem Sci Date: 2017-12-08 Impact factor: 9.825

Review 4. Towards mild metal-catalyzed C-H bond activation.

Review 10. Palladium(II)-catalyzed C-H activation/C-C cross-coupling reactions: versatility and practicality.

Review 5. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp3)-H Bonds.

Review 5. Transition-Metal-Catalyzed, Coordination-Assisted Functionalization of Nonactivated C(sp³)-H Bonds.